CN105745191A - 一种西洛多辛及其中间体的制备方法 - Google Patents

一种西洛多辛及其中间体的制备方法 Download PDF

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Publication number
CN105745191A
CN105745191A CN201480062937.XA CN201480062937A CN105745191A CN 105745191 A CN105745191 A CN 105745191A CN 201480062937 A CN201480062937 A CN 201480062937A CN 105745191 A CN105745191 A CN 105745191A
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compound
milliliters
formula
acid
grams
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CN105745191B (zh
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顾虹
曹剑
陈六杉
黄鲁宁
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Shanghai Kesheng Pharmaceutical Research And Development Co ltd
Zhejiang Huahai Pharmaceutical Co Ltd
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Shanghai Kesheng Pharmaceutical Research And Development Co ltd
Zhejiang Huahai Pharmaceutical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/25—Sulfonic acids having sulfo groups bound to carbon atoms of rings other than six-membered aromatic rings of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/255—Tartaric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Abstract

提供了一种西洛多辛的制备方法。还提供了新的中间体3(7氰基5((R)2((R)1苯基乙胺基)丙基)1氢吲哚基)丙基醇(酯或醚)的有机酸盐和3(7氰基5((R)2(((R)1苯乙基)(2(2(三氟乙氧基)苯氧基)乙基)氨基)丙基)1氢吲哚基)丙基醇(酯或醚)及其盐的制备方法。所述方法的优点在于：原料廉价易得，操作简便，中间体及产品易于纯化，且收率高，适合于工业化生产。

Description

PCT国内申请，说明书已公开。

Claims (11)

  1. PCT国内申请，权利要求书已公开。
CN201480062937.XA 2013-12-09 2014-10-20 一种西洛多辛及其中间体的制备方法 Active CN105745191B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN201310659145.8A CN104693090A (zh) 2013-12-09 2013-12-09 一种西洛多辛及其中间体的制备方法
CN2013106591458 2013-12-09
PCT/CN2014/088953 WO2015085827A1 (zh) 2013-12-09 2014-10-20 一种西洛多辛及其中间体的制备方法

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CN105745191A true CN105745191A (zh) 2016-07-06
CN105745191B CN105745191B (zh) 2019-04-09

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CN201480062937.XA Active CN105745191B (zh) 2013-12-09 2014-10-20 一种西洛多辛及其中间体的制备方法

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Country Status (6)

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US (1) US9745264B2 (zh)
EP (1) EP3081554B1 (zh)
JP (1) JP6248202B2 (zh)
CN (2) CN104693090A (zh)
ES (1) ES2784835T3 (zh)
WO (1) WO2015085827A1 (zh)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2607639B1 (es) 2015-09-30 2018-02-28 Urquima, S.A Sal de ácido maleico de un intermedio de silodosina
CN108033906B (zh) * 2017-12-28 2021-07-06 常州瑞明药业有限公司 一种西洛多辛中间体的制备方法
CN115838349B (zh) * 2023-02-20 2023-07-14 南京桦冠生物技术有限公司 一种3-(7-氰基-5-(2-氧代丙基)吲哚啉-1-基)苯甲酸丙酯的制备方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001199956A (ja) * 2000-01-14 2001-07-24 Kissei Pharmaceut Co Ltd 光学活性なインドリン誘導体の製造方法およびその製造中間体
CN101585798A (zh) * 2008-05-20 2009-11-25 浙江华海药业股份有限公司 光学活性化合物1-(3-苯甲酰氧基丙基)-5-(2-(1-苯基乙基胺)丙基)-7-氰基吲哚啉及其制备方法和用途
CN102382029A (zh) * 2011-07-26 2012-03-21 浙江华海药业股份有限公司 一种西洛多辛中间体成盐制备方法
WO2012062229A1 (en) * 2010-11-12 2012-05-18 Zentiva, K.S. A method of manufacturing (-)-l-(3-hydroxypropyl)-5-[(2r)-2-({2,2,2-trifluoroethoxy)- phenoxyethyl}amino)propyl]-2,3-dihydro-lh-indole-7-carboxamide
CN102702067A (zh) * 2012-06-18 2012-10-03 北京联本医药化学技术有限公司 用于合成西洛多辛的新中间体及其制备方法和用途
CN103396352A (zh) * 2013-08-07 2013-11-20 苏州明锐医药科技有限公司 赛洛多辛的制备方法
CN103420893A (zh) * 2013-08-02 2013-12-04 江苏和成新材料有限公司 制备西洛多辛中间体的方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101993406B (zh) * 2009-08-27 2014-01-15 浙江华海药业股份有限公司 光学活性的吲哚啉化合物及其制备方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001199956A (ja) * 2000-01-14 2001-07-24 Kissei Pharmaceut Co Ltd 光学活性なインドリン誘導体の製造方法およびその製造中間体
CN101585798A (zh) * 2008-05-20 2009-11-25 浙江华海药业股份有限公司 光学活性化合物1-(3-苯甲酰氧基丙基)-5-(2-(1-苯基乙基胺)丙基)-7-氰基吲哚啉及其制备方法和用途
WO2012062229A1 (en) * 2010-11-12 2012-05-18 Zentiva, K.S. A method of manufacturing (-)-l-(3-hydroxypropyl)-5-[(2r)-2-({2,2,2-trifluoroethoxy)- phenoxyethyl}amino)propyl]-2,3-dihydro-lh-indole-7-carboxamide
CN102382029A (zh) * 2011-07-26 2012-03-21 浙江华海药业股份有限公司 一种西洛多辛中间体成盐制备方法
CN102702067A (zh) * 2012-06-18 2012-10-03 北京联本医药化学技术有限公司 用于合成西洛多辛的新中间体及其制备方法和用途
CN103420893A (zh) * 2013-08-02 2013-12-04 江苏和成新材料有限公司 制备西洛多辛中间体的方法
CN103396352A (zh) * 2013-08-07 2013-11-20 苏州明锐医药科技有限公司 赛洛多辛的制备方法

Also Published As

Publication number Publication date
EP3081554B1 (en) 2020-04-08
EP3081554A4 (en) 2017-08-16
WO2015085827A1 (zh) 2015-06-18
CN104693090A (zh) 2015-06-10
EP3081554A1 (en) 2016-10-19
JP2017502009A (ja) 2017-01-19
US20160304452A1 (en) 2016-10-20
ES2784835T3 (es) 2020-10-01
CN105745191B (zh) 2019-04-09
JP6248202B2 (ja) 2017-12-13
US9745264B2 (en) 2017-08-29

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